As I Journey Onward

I have talked about how young I was when I first Cross Dressed at the early age of 10 before becoming a Drag Queen, also at a very early age. Between the two I am proud to admit and say out loud that they are my life and there’s nothing in this world that can change that for I wouldn’t allow it for a minute. There has been some heart breaks along the way and I am sorry for that but there’s nothing I can do about the past other than journey onward.

Here’s the thing, I don’t believe that one day when I was 10 years old I just decided to dress up like a girl. I don’t believe that anyone one of us would begin setting ourselves up for the diversity that was soon to come. What I mean by that is who in their right mind would want to begin a process of being humiliated, become an outcast, hated, slandered, judged, disowned, scrutinized, labeled, threatened with violence, made fun of, listen to derogatory comments and so much more? No I don’t believe that anyone wishes that upon themselves. I think for most of us fear began to envelop us and prevent the inevitable which was coming out, standing tall and proud to present ourselves for who we were and where we wanted to be.

With me there were multiple adversities associated with who I was and who I am now. I not only blossomed as a cross dresser and drag queen but quickly realized also that I was gay as well. I As I get older I look back and the memory of my mother coming to the realization that her only son and youngest of my family preferred to wear female attire and sleep with the same sex had to be devastating for her. She had to somehow accept the fact that I would never give her a grandchild as she hoped for, that people would question how she raised me and so forth. That said in hopes to please her and the rest of my family I decided to try another journey or avenue by going straight and getting married to two different women. Needless to say neither worked out. The mental, physical, emotional and spiritual remnants of who I really was remained intact. In other words I was still the girl I had discovered I was and missed trying to be. While in the short time I was married to both of them I continued to cross dress and was also very unfaithful by continuing to go to bed with men when I could. I didn’t set out to hurt anyone like I did but it happened. I was caught by my second wife one day when I was wearing only a bra, a garter and stockings, makeup, my hair all teased out and a pair of her stiletto’s I had made a point of buying for her so I too could wear them. That began the process of what was to be my second divorce and outing.

The thought that one day I just decided to begin cross dressing to accommodate this girl that lingered inside of my mind and body is so ridiculous. I believe wholeheartedly that I, or we, are simply born this way. No one on their best day would subject themselves to live with so many secrets or receive the treatment by society that so many of us experience. I can remember when I started wearing makeup openly. I would wear it so lightly I thought that people wouldn’t notice but as with any other secrets we hold, the more we get away with the more we do. In my case it was wearing a little more makeup every day until it was finally recognized by others. That was when my secrets began to transpire. I was teased, threatened and humiliated by kids at school. I backed off for a while but the fact that I had been exposed didn’t go away. One day it was thoughts of telling all and the next day was deciding to make my greatest attempts to keep it all within myself and the dark lonely closet. Neither of my desires to wear makeup and dress everyday, once I was home and by myself, vanished.

So I do believe I was just wired this way at birth and when it was impossible to ignore it I participated and went forth with what felt right. My journey continues today only there are little to no secrets in my life. I know nothing I do still today will ever change. I am now at an impasse with myself or in the checkmate status and it is somewhat difficult to decide if I want this journey to continue with HRT treatment or do I just keep doing what I have always done? If I do decide on HRT I know it won’t be from choice but instead be something I am bound and destined to do. It takes a lot of courage and commitment to do what we do. My first drag mother/mentor once told me that “anyone can put on a dress but, it’s how you wear that dress that counts”. So with this said my journey that began so very long ago continues onward and I am not going to go against who I was born to be!

Jackie Wild

Jewelry Artisan, cocktail waitress, part time escort. at Emerald Club, Shuckeys Club

Hello I’m Jackie. I had a pretty long bio and decided to shorten it up. Most of you here at CDH know me, those of you who are new to CDH I say hello to you and welcome to a family you won’t know elsewhere. I love to talk so should you feel the need just hit me up, I’m here!

There are those who claim to accept crossdressing, and say that others should be allowed to do what they...

31 Comments

Peggy Ann Culpepper2 months ago

Way to go Jackie, thank you for telling it like it is, as you say it aint easy being who we really are. even todays world condems us, but think what i would have gone through and did in my mind growing up in the 40’s and 50’s. i think that i would have died had i been caught and exposed growing up. I was actually caught when i was ten years old, the first time that i can remember wearing panties , I was staying at an Aunts house a few days, and there were three girls and one boy cousin . I had only one brother so being in a house with girls that left panties on the floor in the bathroom was heaven that i had not known before.
Anyway, i wore the panties under my jeans during the day and then they felt so fantastic, i thought that i could get by sleeping with them under my PJs. That was great untill my male cousin, with whom i had to sleep with saw the panties sticking out above the PJs.
I really thought that i would die right then and was actually ill from shame the entire next day. My cousin never, ever mentioned seeing the panties and actually kept me from growing up with the stigma that would have gone with it. i will always consider him a Saint and i know that he is in heaven now smiling at my confession.(He actually grew up and became a Baptist Preacher. I will always be grateful to him for what he did for me.
i am grateful to You Jackie for Your story and to Vanessa and all the Wonderful Girls at Crossdresser Heaven for allowing us to tell our CD Stories.

I’m just curious as you consider yourself gay. Are you attracted to women? I’ve come to the personal acceptance that I am bisexual but most female centric. I’ve had sex with a few men but it was mainly sexual not emotional. Do you have that emotional connection with men you date? Personally I love my wife and am fulfilled by being with her. Although when I told her I crossdressed she asked me if I wanted to have sex with men. My mom asked the same vCard thing when I came out. Just curious how it was for you?

Victoria I think for actually ass nine reasons people automatically believe that a cross dresser, a drag queen and any other time a male puts on women’s clothing that they are gay or bi and want to be with men sexually or intimately. It’s just the way our society thinks. It was one of the first questions I was asked from my sister’s and a good friend when I was giving up the fight of the dreaded closet. Are you gay, have you been with a guy and so fourth. My best friend who was a girl asked me that one day after I admitted everything to her. She even asked me what it was like to be with a guy because she was still a virgin. For me personally the answer was “I’m pretty sure I am gay” I had been with two different guy’s, both times I had enjoyed the experience so it was safe for me to say yes when asked. For all the right reasons there was no question in my mind. Yes I had attraction for certain females but it was never sexual. My attractions were more towards what some wore, how some carried themselves, how some spoke, how certain one’s wore they’re makeup and so on. I came out when I was around 14 and although it was a bit scary it was the best decision I had made in my short lived life. It’s amazing how much people already know about us when we think we are being so secretive. For me it became overwhelmingly obvious to anyone who knew me or walked into my bedroom, it had the very obvious surroundings, like a teenage girls room and not a boy’s room. As far as the emotional connection with guy’s I date or choose to sleep with I would have to say yes, and no. Some guy’s I may be extremely attracted to and have every immediate intention on going to bed with before the night is over while other guy’s I may not and just go out with them to have some fun. I hope what I have said here helps you determine what you feel. Also I’d like to say that I think a person just knows when they are attracted to anyone, opposite or same sex. I truly believe that the time will come when a person can openly say or admit they are attracted to the same sex and nothing bad will be felt about. While our society get’s closer each day with acceptance, whether it be sexuality, cross dressing, or simply being who we are and were born to be it’s my hope that anyone who fear’s being themselves be gifted a spiritual experience and given the courage to live they’re true identities. Life is too short to live in fear!

I wouldn’t worry. It can be confusing. I think you just have to say to yourself, “This is something that’s a part of me.” For me it was understanding I not a binary gender. Accepting I’m a part of both genders. I see things in ways and feel things in ways 99.999% of the population doesn’t.That unique awareness makes me who I am a better person. Only through self acceptance and love of yourself can you truly love someone else. I hope you find solace because this Journey we are on is not easy but hard. It’s the Journey that rewards us. The destination is life.

I guess I should be honest with you. I have a hot fetish for pantyhose and high heels. I enjoy the feeling that the smooth and silky nylon clinging to my legs excite me. The other is the intensity of my favorite high heels. I have many pairs of high heels and intend to have even more. Lingerie, the ultimate in the feminine looking lifestyle is a very erotic sensuously beautiful and pretty extension to the full on look we are seeking as well.

I absolutely love the feminized girl I’ve become. The realization that I am a beautiful person who loves to wear my own personal attire. We are all about the feeling that you love when you dress up as a girl in our pretty silky lingerie and high heels. I enjoy the way I look and feel in the sexy outfits and the other ways of doing it for the intended purpose of the sheer enjoyment of my feminine lifestyle.

Jackie, Thank you for a well written post ! many of your Posts have made me feel better on my life style and my dressing. I have found that better place and continue on my journey as many of the girls here. However, I cant continue with HRT so my journey will
have to continue as is the best I can no if , and or butts. Thank you from the bottom of my heart.

Thank you Jackie your words are so inspirational to all of us. I to continue my journey in life for I am now on HRT and will be for the rest of my life. I knew at a young age this is what I wanted and so wish I could have found a lot of thing out earlier then I did but life has it twist and turns and we still end up where we belong some how. Wishing you the best in your life journey.

Jackie you are a true inspiration for the rest of us sisters! I just LOVE your writing style too, you are very good with words.
I agree completely with you, we were this way at birth, no other reasoning makes sense as none of us no why we are the way we are.
How true that none of us wish to be ridiculed or worse, but we cannot stop being our girl selves no matter what.
I loved your last statement about wearing the dress – so true!!
Please write more, your amazing and adorable!
Hugs and kisses, Angela

Ahhh thank you so much Angela for the kind words and compliments. You brought a tear to my eyes (but I know you didn’t mean to haha). You really know how to make a gurls day. I hope your day brings all the majik you ask for and deserve, Jackie….

Dear Jackie, I am new to this site and I must agree, your life is very inspirational and gives me the courage to continue with my path. I also realized by age 6 that I was not the gender my body said I was. I also wore my mom’s bras and panties whenever she wasn’t home wash cloths and all for breast size.I had 4 failed marriages cause I could never be the “man” they wanted. I was unhappy and empty. Now at 63, I have found my happiness and inner peace as a cross-dresser. This is long, sorry. I can so relate to you and Thanks for sharing your life with us!

Hi Rymi, I want to thank you for the lovely comments and compliments. You may be 63 but as long as you have found the inner peace you long for you cannot go wrong by following your heart and going for the ultimate experience of mastering your quest, You are a true inspiration for others who may feel they are getting older and haven’t found their place yet. May your awesome journey stay bright and new each day, Jackie.

Thank You Jackie for your kind words, truly they Do mean a lot to me and so many others. As age creeps up on us we try to find inner peace and happiness within our heart and soul, when were we the most fulfilled and the happiest? For me it is being a woman! This is when I am the happiest and so one with my body, mind and soul ! I just can not ever see me as a male ever again. Life is hard enough for us woman but to have to lose my womanhood and be a male again would just destroy me! Like now, I’m in my silky nightie, nails are painted a baby blue and I am in heaven typing this to you. I truly love my life finally and honored to call you a sister!

Thank you for your life story and you sharing your journey. I like statement at the end “anyone can put on a dress but, it’s how you wear that dress that counts”. I think that means a lot to many of the ladies here at CDH.

Dear Jackie, I very much enjoyed your article. You’ve had quite a journey. You’re very strong, and that strength has carried you through and will carry you as you step by step enter your future.
Take care, pretty lady.

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